Surfer Sally

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Never be embarrassed about this thing Toby, you are a lucky guy."

She stood back up and pushed him back on the bed. He crawled to the center and just stared at her.

"Are you really that excited already?"

"You have no idea, my heart is racing."

"Ok, you know about the sixty-nine position right? Well I'm going to blow you, and you can cum in my mouth, but with her, if she goes down on you, warn her or stop her before you cum. If she wants it in her mouth, trust me she will go right back after it. But just blowing your wad in a girls mouth is rude unless you know she wants it, ok?"

"Ok, wow, I figured if she was doing it..."

"Ya, you were wrong, most girls want to suck on it, but not all of them want to swallow your load."

She climbed on the bed and straddled his face and then grabbed his cock. It twitched in her hand.

"So this is what I should try and do first?"

"No, this is to calm you down, next you'll learn what a woman likes. For now, just lick my gash and try not to cum."

She slipped his cock in her mouth and avoided the head as much as she could for the first few minutes. He was actually pretty good at eating pussy, and if he spent just a little more time on her clit she could cum.

She started sucking harder and rubbing her lips on his crown and he started moving his hips towards her mouth.

"I'm gonna cum!"

She lowered her mouth until he entered her throat and started humming. She felt his cock pulsate as the cum rushed from his balls and into his cock. She lifted up and slid back down and it started blasting into her sucking mouth.

She sucked him dry and then turned so she was on her back. He was breathing heavy, and she rubbed his chest while he caught his breath.

"So was that what you expected Toby?"

"My...god...my...toes...curled."

"Good, I'm glad I haven't lost my touch."

"No, you haven't lost anything."

"Ok, so later today you get her in your room. And trust me, she will want to be in here. You will both be wearing bathing suits. You just drop your trunks and put on a pair of shorts. Let her see your cock, ok?"

"Are you serious?"

"Yes, she wants to see it, she just doesn't want to feel like she has to service it right away. Let her see it and then put it away."

"Man, ok...what next?"

"You will probably end up making out on the bed, so after a little while start rubbing her breast through her top. If she doesn't remove it, ask her if you can."

"Got it, what next?"

"Kiss your way to her breast and then take her nipple in your mouth. Go ahead and get mine."

He covered her nipple with his mouth and started sucking and nibbling on it. He didn't need any practice at this step.

"Don't ever bite unless you're asked to. It can hurt for days afterwards if you're too rough. Make sure you play with them both, because on some girls one might be more sensitive than the other. My right one is twice as sensitive."

He switched to the right one and she started moaning. He was playing with the hoop in his mouth and pulling on it with his tongue. She stopped him while she tried to catch her breath.

"Ok...so she will probably still be wearing her bottoms, so if she responds well to your mouth on her breast, try running your hand down her stomach. If she squirms or grabs your hand it's too soon. That isn't going to happen though, because this girl wants you, and she's waited a long time for this."

"So I just rub the front of her suit, just trying to be gentle?"

"Yes, and by now she should be getting excited so run your finger under the waistband, but don't go down right away. You'll know if it's the right thing to do."

He slipped his hand between her legs and she opened them. He started rubbing around her pussy and she urged him on.

"Ok, ok, so you get her hot and bothered, and she helps you slide them down. Tell her it's beautiful, tell her it's amazing. Don't call it anything, not yet. Girls are nervous when a guy see's their pussy for the first time, especially if you're the first guy to ever see it. It's everything to them, so tell her it's incredible, make her feel special."

He crawled between Sally's thighs and it was incredible. It was wet and pink, with dark edged lips hanging open, and Toby dropped his mouth down and licked her from the bottom to the top. At this point she just let him do his thing for a while. He rubbed the sides of her clit and fingered her pussy and when he sucked on her clit she exploded.

"Oh fuck, ya, ya, ya, suck my clit!"

He was exploring her pussy with two fingers and when he got lucky and bumped her g-spot she gasped and started grabbing his head.

He figured out what he'd found and paid extra attention to it. Her orgasm got stronger and she begged him to fuck her. He crawled between her legs and grabbed his cock.

"Ok, don't just shove it in, even though that's what I really want right now. Rub it between my lips a few times, tease me with it. Put it in an inch and then rub some more."

He teased her until she told him she wanted him inside. He stuck the head in and started sinking deeper.

"Ya, nice and slow and steady, it feels so good. You have a nice cock Toby, trust me."

Toby realized when she started moaning, that he was in control. He started a slow rhythm and started fucking her deeply. He grabbed her leg and hooked his arm behind it and his cock started reaching deeper. She started moaning louder, so he started fucking faster.

"Oh, oh, oh, ya, faster Toby, FUCK ME HARD!"

He started pounding her pussy as fast as he could and she yelled out as she started bucking and cumming under his cock. He grabbed her second leg and pushed it up as he continued his assault on her wet cunt.

He slowed down when she stopped thrashing and bucking up against him, and she told him to let her turn over. She got on her knees and he returned to fucking her quickly.

"Now grab my hips and fuck me until you cum Toby!"

He liked this position and got right into it. She hadn't planned on cumming again so soon, but he was seriously fucking her. She started moaning out that she was cumming again, and he started grunting with each stroke.

"God I love fucking, I'm going to cum!"

"Fucking cum in my cunt!"

He grunted hard and loud and she felt him unload inside her. She squeezed his cock while he pumped as much cum as he could muster, inside her. Sally fell forward laughing, and he fell to his butt.

"Ok, so you have the sex down pat, trust me, Robin's a lucky girl."

She got up and told him to shower and then clean the pool. He jumped up, and then stopped and turned to her.

"Sally, thank you, you are beautiful, and sexy, and...the coolest."

For the first time in ages, she blushed. She felt young, and completely satisfied. She smiled as he left the room for the shower.

At ten to twelve Robin arrived with a bag full of food. She'd made sandwiches and a salad. She was bubbly like the day before, but the first thing she did once she set the food on the table was plant a kiss on Toby. It wasn't just a peck, it was a "Remember me, I let you play in my bra" kiss.

Sally set the table and then sat down across from Robin. Sally was wearing a tight white t-shirt with a Billabong logo across the front and being braless, her piercings showed.

"Are your...nipples pierced Sally?"

"Yup, are yours?"

"N...no, didn't that hurt?"

"It did at the time, but it's so worth it, trust me."

"A friend of mine, you know her Toby, Julie Watts, she has hers done."

"Julie Watts has pierced nipples?"

"...and she has one down below."

"I had my hood pierced, but it was too much with a wetsuit on most of the time."

Robin's cheeks were red but she was smiling as she ate her sandwich. Sally smiled and finished her lunch before helping clean up and then going to the back yard.

"Sally is really cool, You must really enjoy her being around."

"I do, and she really is a cool woman."

"Does she...go topless in the pool?"

"She did yesterday, but I don't know about today."

"Wow, she's just...so great."

Toby went to the linen closet and grabbed a stack of towels and then went to the pool. Sally was stretched out on a lounge chair still in her t-shirt but she'd removed her shorts.

She had on the smallest little bikini bottom Toby had ever seen. It just barely covered her still swollen pussy. He figured the back was just a string in the crack of her ass. But when she got up, it was actually a small strip that just barely covered the edges of her crack.

Toby sat down on a chair and pulled his shirt over his head. Robin walked behind him and rubbed his shoulders and then ran her hands down his chest.

"Are you coming in the water with me?"

"I should toss you in, that would be fun."

"You wouldn't dare!"

She jumped away and skittered around the pool to the far side. Sally laughed as Toby ran after her. She was pretty quick and kept the pool between them. Toby gave up and walked casually back to his chair, but when Robin thought he was getting ready to sit down and approached him he turned and took her into the pool with him.

Sally was curious what her reaction would be, and it was adorable. She wrapped her arms around him and kissed him like they were alone in the yard. When the kiss ended they started playing around with a ball for a while.

Robin was wearing a cute little string bikini. It was pink with white flowers on it. She swam up to Toby and tried pushing him under water by climbing up his body. He pushed her up and away sending her flying. She splashed into the water and when she came up one side of her top was above her breast.

She smiled as her cheeks turned red and then pulled both sides up for a second and then back down. She started laughing and swam back to him.

Sally sat up and pulled her shirt over her head and then dropped back down and closed her eyes. Robin looked over and her mouth opened when she saw Sally topless. She started whispering to Toby.

"She's topless, that's so...cool."

"She spent a lot of time out of the country; I guess it's pretty normal in some places."

"Do you like her piercings?"

"I think they're pretty cool."

"Would...mine...look cool like that?"

"...very cool..."

He had moved to the shallow end with her legs wrapped around his waist, and he was amazed at how well he was keeping his cool.

"Toby, how come this took so long to happen, was it...me?"

"No, I was scared of...rejection I guess?"

"God, I've liked you since...forever I think."

"I...I'm sorry, I was so...scared to lose a friend."

She leaned in and started kissing him and his hand went to her butt. She grabbed it and he panicked at first, but she moved it to the front of her bikini bottoms. She rubbed his hand across her crotch and then pushed his hand into her bikini bottom.

She let go and looked back where Sally was sunning and looking away from them. His finger brushed her clit and she shivered and turned back to his mouth. His finger slipped inside her and she moaned out quietly.

"Do you want me to remove my top?"

"Uh huh..."

She pulled the string behind her back and slipped it over her head. She tossed it on the deck and his mouth covered her nipple.

"I can't believe we're doing this in front of her."

"We can go to my room."

"No, this is fun, I want to swim topless a little."

Her hand slipped up the leg of his trunks and she grabbed his semi hard cock. He gasped and then returned to her nipples. She released him a second later and swam away. She blew him a kiss as she glided backwards on her back with her perfect tits out of the water.

"I think I'm a bad influence on you."

Robin looked up at Sally who was sitting up and watching her.

"Actually, it's pretty liberating. We went to Greece last year, and everyone was like this, even younger girls."

"Ya, I went to a few nude beaches over the years."

Sally looked at Toby and he smiled. She stood up and removed her tiny bottoms and then returned to sunning.

"This is liberating."

Robin looked at Sally sprawled out on the lounge chair and then looked at Toby. He chuckled and grinned. Robin looked around and then a few seconds later her hand came up with her bikini bottom in it.

She looked at him like he was now over dressed. He slipped his trunks off and showed her. She swam over to him and settled in his lap.

"I've, never...you know, I..."

"Do you want to go to my room now Robin?"

"Ya, I think I do."

They got out of the pool and ran to the house. Sally started laughing and her fingers wandered between her thighs.

"It's about time..."

Toby followed her naked butt up the stairs. Her pussy was amazing looking, and the lips were void of hair. She had hair above her pussy, but that was it.

She jumped on his bed and watched him walk in the room. He stopped beside the bed and let her stare at his cock. She moved to the side of the bed and wrapped her hand around his cock and it grew hard in her fist.

"I've never done this before, so..."

He watched as she leaned forward and took his head in her mouth. He was thankful he'd already cum twice that day, because he didn't want this to end. She fumbled around and got him with her teeth twice, and he loved it.

She pulled away and he crawled on the bed. Her arms went around his neck as he moved in to kiss her mouth. She was aggressive and soon she was trying to get him to move between her legs. He broke away and crawled between her thighs.

She watched in amazement and gasped when his tongue slipped inside her sopping wet pussy. He slipped a finger inside and it felt completely different than Sally. He turned his finger up and started rubbing around and her fingers found his hair.

"God you're beautiful Robin."

She whimpered and he started licking the sides of her clit. Her hips started moving around and she let out a moan. He sucked her clit into his mouth and rubbed his tongue against the sensitive tip.

She started shaking under him and she said his name. He'd never loved the name so much as at that moment. He rubbed harder with his finger while he battered her clit.

"Oh...MY...GOD!"

Her hips started thrashing around and she let out a moan and then she started gushing in his mouth. Her hips were humping at his face and her hands were rubbing his head around. He eased his attack on her senses and then lifted his head to look at her. She had tears in her eyes but she was smiling with an open mouth.

"That was unbelievable Toby, my god!"

He crawled up to her face and she started kissing the wetness from his lips and cheeks. He found her nipple with his fingers and played with it until she let his face go.

"I've been on birth control for three years, so we can...if you want to?"

"Are you sure, because...I am?"

"I've dreamed about this moment for two years Toby, and it's already more incredible than I ever dreamt it would be."

"Are you a...virgin?"

"Not really, I broke it last year."

He lifted up on his knees and she pulled her knees up and spread them.

"Is it really pretty...down there?"

"Oh my god, its...incredible. I've tried to picture it in my head, but I never even came close."

"You've envisioned...my pussy?"

"Too many times to count."

He slid closer and teased her with is cock and she moaned out. He leaned in and the head slipped between her swollen lips. It was tight, way tighter than Sally. He slid in a couple inches and her back arched.

"Oh wow...that's..."

He kept pushing until he was bottomed out and he dropped down to his hands and then to her chest. He started a slow fucking and she grabbed his shoulders. He was pushing deep and grinding his pelvis into her clit and she was moaning and rubbing his ass.

"My god Robin, you feel incredible."

"I'm gonna...cum...again."

He started fucking her faster and she started digging her nails into his ass pulling at him. He reached down and grabbed her leg and pulled it up. He started lifting up and hammering down into her and she started grunting and rolling her hips into his thrusts.

"I'M CUMMING TOBY, FUCK ME!"

He started grunting and pounded her quivering pussy as hard as he could and then he exploded, filling her with his cum.

"My god, it...won't...stop...my...orgasm."

He kept pumping until he started going soft and then rolled off of her.

"That was the most incredible moment of my life Robin."

She was still trying to catch her breath but she rolled on her side smiling through glassy eyes.

"You were amazing Toby..."

She moved to his stomach and then without warning she took the head of his cock in her mouth and sucked the last bit of cum from him. It was like a taste test. She moved back up beside him and grinned.

"Maybe next time you could...cum in my mouth?"

"Oh god, I'm in love."

"So am I Toby, with you. I have been since I was little."

"God, remember back in grade school, we used to fight all the time."

"Ya, you said I had cooties."

"Well I love your cooties now; I'll eat them every day."

"Your mom never gets home before seven, right? So we have the house to ourselves."

"Yes, but my mom wouldn't care if we were in here with the door closed."

"Toby, was this your first time?"

"Wow, well...no."

"So how many times before today?"

"Once, and it wasn't like this, trust me."

"Who was it with?"

"I shouldn't say, it wouldn't be right."

"So...are we together now?"

"For as long as you'll have me Robin. I've loved you for as long as I can remember too."

"Toby, was it Sally, did she make all this happen?"

"Yes, she forced me to call you last night, and when I told her I was scared, she showed me how not to be. If she hadn't forced me, I'd still be hoping someday we'd be together."

"I'm gonna thank her, she's just...amazing."

"So you're not upset?"

"It's only me from now on, right?"

"It was only you even then. I wanted you to be happy when this happened, I didn't want to disappoint you."

"You didn't, you definitely have to do that mouth thing, a lot."

He started laughing and she crawled to his mouth and started kissing him again.

Tuesday evening when Toby's mom got back she found the three of them watching TV. She put her bags in her room and then joined them. Toby was laying down on the love seat and Robin was next to him under his arm. She smiled at Sally and kicked her shoes off.

"How was your trip mom?"

"Long and boring, as usual, it looks like you two finally got it figured out."

"Uh huh..."

Two hours later Toby and Robin got up and Robin said goodnight. Toby said he was taking her home and they walked out the door together. Toby's mom got up and looked out the window at her son.

"So how did it go Sal?"

"You have one hell of a son, let me tell you."

"So did you...sleep with him?"

"Once, that's all it took. He'll be fine now; he has confidence, and a very open minded girlfriend."

"I can't believe I set him up like this, what kind of mother does that?"

"The good kind I figure, she knows about it, she doesn't care, she even thanked me. Apparently he's pretty good."

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
AnonymousAnonymousover 8 years ago
This Was...

...really nice!

xx

AnonymousAnonymousover 8 years ago
:)

Great job. It certainly made me smile. Nice surprise ending. Thank you.

clackormanclackormanover 8 years ago

Oh to have had a mom and a friend of mom's like that! Great story line. Well written. Nice surprise ending. I will look forward to further contributions from you!

AnonymousAnonymousover 8 years ago
At last

Toby and Robin finally connected with the help of an older friend. With a little experience anything can happen . At long last.

AnonymousAnonymousover 8 years ago

Good story with a bit of everything. Well written and a cute surprise ending that I didn't pick. Five stars.

Share this Story

Similar Stories

My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
On The Train Young man and mature woman connect on daily commute.in Mature
After School Special Todd's mistake gets surprising results from Miss Ross.in Mature
Neighborhood Milf Life long dream fulfilled when he has her.in Mature
Snowed In with the Boss Getting snowed in with the bitch boss turns into a surprise.in Erotic Couplings
More Stories